In 2005 Automattic was small. Through some miracle I had convinced Donncha O Caoimh, Andy Skelton, and Ryan Boren to leave their safe jobs, join a company with almost no money in the bank run by someone with no experience, and whose core idea was to give away and open source all our core IP. There were more questions than answers. Would a hosted version of WordPress move beyond the geek appeal the OS project had? How would the virtual company with no office work? Could we develop a service alongside an OS project without screwing both of them up? Should I raise money? Most importantly, would it scale?

In 2006 we developed a series of answers (sometimes hard-learned) to those questions. WordPress was obviously limited by its installation requirements — when it was added as a one-click to web hosts and when WordPress.com (and other MU hosts) made it simple to get a blog the popularity grew beyond what I could have ever imagined. In the WordPress.org world it wasn’t perfect — I consider the long period between versions 2.0 and 2.1 a personal failure — but after that initial bump the development really picked up and the community and usage exploded. There have been 5,880,790 downloads of WordPress.org since Automattic started. (3,852,554 in the past year alone.)

We ended up raising a small amount of money (1.1 million) to allow the company to take some risks without worrying about payroll but we ended up using very little of that capital because revenues grew quickly, allowing us to remain break-even even as the team scaled to 18 full-time folks and a number of contractors. Toni Schneider left Yahoo to join as CEO, a partner I couldn’t imagine getting along better with, and we started to look like a real company despite having no office and some of us never meeting in person.

Fast forward to 2007: many of the seeds planted started to really bloom. On WordPress.com 1.8 million new users joined, they created 25 million posts, we served 3.2 billion dynamic pageviews, and grew to reach over 100 million unique users worldwide. Akismet blocked billions of spams from reaching blogs. Nearly every major media organization, from the NY Times, WSJ, CNN, Fox, Time, People, and more, have embraced WordPress. Finally the approach of serious acquisition or majority-stake investments brought up the biggest question we’d faced so far: should we sell, or build out Automattic to be an independent company for many years to come.

That decision actually wasn’t hard. I couldn’t stop thinking about the opportunities and it became clear that the road ahead was much longer than the road behind us.

That brings us to today. The New York Times, the flagship of media, is joining our existing investors Polaris, True, and Radar in expanding their minority stake in the company. Automattic is now positioned to execute on our vision of a better web not just in blogging, but expanding our investment in anti-spam, identity, wikis, forums, and more — small, open source pieces, loosely joined with the same approach and philosophy that has brought us this far.

Automattic.com is no longer a placeholder, it now has a bit more info about the team behind WordPress.com and Akismet. This is what I’ve been working on since I left CNET. The site is still just a shell though, a lot more tidying up to do there. Your mileage may vary. (Should we call it Beta?) This week is pretty jam-packed with announcements, so stay tuned. 🙂

The timing for the interview couldn’t be better. As people watching closely may have already started to notice, About.com has begun switching their sites over to WordPress from Movable Type. They’ve been doing it quietly and one-by-one for at least month now, you can see WP in action on Weblogs, Baby Parenting, entrepreneur, US politics, and many more. They’ve integrated it so tightly with their system most of the usual signs of a WP blog aren’t there, but the dead giveaway is the comments. In fact none of their older blogs seem to have comments enabled, just the upgraded WP ones.

About.com isn’t very “2.0” hip but they are still get some of the highest traffic on the web, easily within the top 50 sites in the world. From what I understand they haven’t made any changes to the core code, all of their customizations have been through plugins. They’re also looking at bringing a WP “powered by” link to the pages. (Which, as noted in the previous entry, is completely optional.) I’m very glad About has found a platform that will grow with them. 🙂

It was just about a year ago I blogged about leaving Houston and driving across the country to join CNET. It ended up being one of the best moves of my life. Since moving to the Bay Area I’ve had incredible oppurtunities and met a whole tribe of amazing people. For what I’m passionate about, I really believe this is the best place in the world to be.

For me the last year has really been about learning. From school in Houston to CNET to the explosive growth of WordPress and Ping-O-Matic, it’s been an incredible ride. There have been plenty of mistakes along the way, but all-in-all I don’t mind because that’s when I learn the most. At CNET I was lucky enough to be surrounded by veterans of the industry whose success and perserverance through the thick and thin of creating what we know as the web had a deep impact on me. CNET also gave me incredible flexibility to work on WordPress, and has embraced WP all over their organization, it was really the ideal gig.

However in the back of my mind I was wondering if I could focus on my passions full-time, to put more daytime hours into the community and projects that have changed my life already. I don’t need much, and working on WordPress full-time is my idea of heaven. I gave notice (they’ve been incredibly supportive).

I could say this was a hard decision, but the truth is I can’t imagine myself doing anything else.

Watch this space, I’ll have plenty more to talk about in the next few weeks. I’m very excited about the things happening with WordPress.com, WordPress.org, bbPress, a WordPress non-profit, Ping-O-Matic, and a few projects so shiny they don’t even have names yet.It’s a little scary to be leaving the safety net, but nothing worth doing in life is without risks.

My last day at CNET is Friday, October 21.

If there is ever going to be a time in my life to take big risks and reach for the brass ring, now is it.